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tert-Butyl ((4aS,5S,7aS)-7a-(2-fluoro-5-nitrophenyl)-5-(trifluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)carbamate → tert-butyl[(4aS,5S,7aS)-7a-(5-amino-2-fluorophenyl)-5-trifluoromethyl-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl]carbamate

HRID 2045846
ノート
印刷プレビュー

反応式

HRID 2045846 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[C@:11]12[CH2:19][O:18][C@H:17]([C:20]([F:23])([F:22])[F:21])[C@H:16]1[CH2:15][S:14][C:13]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[N:12]2.O.O.[Sn](Cl)(Cl)(Cl)Cl>C(O)C>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([C@:11]23[CH2:19][O:18][C@H:17]([C:20]([F:23])([F:21])[F:22])[C@H:16]2[CH2:15][S:14][C:13]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[N:12]3)[CH:4]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 68171523tert-Butyl ((4aS,5S,7aS)-7a-(2-fluoro-5-nitrophenyl)-5-(trifluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)carbamateHCID 85782573Tin tetrachloride dihydrate

生成物 1

HCID 68171522tert-butyl[(4aS,5S,7aS)-7a-(5-amino-2-fluorophenyl)-5-trifluoromethyl-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl]carbamate収率 99.9%

試薬・触媒・溶媒 1

HCID 702Ethanol
溶媒

実験手順

tert-Butyl ((4aS,5S,7aS)-7a-(2-fluoro-5-nitrophenyl)-5-(trifluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)carbamate (16.61 g) was dissolved in ethanol (250 mL) and tin chloride dihydrate (25.0 g) was added. After stirring at RT for 18 h, the solution was poured onto NaOH (2N aq., 300 mL) and Celite® (˜50 g) was added. The resulting mixture was filtered through more Celite® and extracted with EtOAc (2×500 mL). The combined organic portions were dried over MgSO4 and evaporated to afford the title compound (15.52 g). This material could be used crude but a portion was purified by silica gel column chromatography (20% to 50% EtOAc in hexanes) to afford pure material (recovery 79%). 1H NMR (400 MHz, CDCl3) δ ppm 1.53 (s, 9H), 2.77 (d, J=14.4 Hz, 1H), 3.09 (br. s., 1H), 3.46 (br. s., 1H), 3.62 (br. s., 2H), 3.87 (br. s., 1H), 4.61 (d, J=8.6 Hz, 1H), 4.71 (br. s., 1H), 6.61 (br. s., 2H), 6.85-6.95 (m, 1H)

後処理

  1. additionthe solution was poured onto NaOH (2N aq., 300 mL) and Celite® (˜50 g)
  2. additionwas added
  3. filtrationThe resulting mixture was filtered through more Celite®
  4. extractionextracted with EtOAc (2×500 mL)
  5. dry with materialThe combined organic portions were dried over MgSO4
  6. customevaporated

出典と根拠

ORDレコード
ord-58ab187be9fc4f1ba9c8e59b428f3431
出典データセット
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08592408B2

反応ノート

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